A lignoid glycoside and dimeric phenylpropanoids from Daphne oleoides

Three new natural products, a lignoid glycoside 1 and two dimeric phenylpro panoids 2 and 3, along with two known lignans 4 and 5, were isolated from t he BuOH- and CHCl3-soluble fractions of the whole plant of Daphne oleoides (Thymelaeaceae). The structures of the new compounds were established by sp ectroscopic techniques, including 2D NMR, as 4-(beta -D-glucopyranosyloxy)- 9'-hydroxy-3,3',4'-trimethoxy-7',9-epoxylignan (1), (1R,2S,5R,6R)-6-(3-ethy l-4-hydroxy-5-methoxyphenyl)-2-(4-hydroxy-3,5-dimethoxyphenyl)-3,7-dioxabic yclo[3.3.0]octane (2) and (1R,2S,5R,6S)-2,6-bis(3-ethyl-4-hydroxy-5-methoxy phenyl)-3,7-dioxabicyclo[3.3.0]octane (3). The other lignans were identifie d as (+)-pinoresinol O-(beta -D-glucopyranoside) (4) and (+)-medioresinol ( 5).